Hydrochloric Acid → HCID 70432418, compound

HRID 986549Notes

Reaction equation

HRID 986549 reaction equation
[CH:1](/[C:14]1[CH:25]=[CH:24][C:17]([CH:18]=[CH:19][C:20]([O:22]C)=[O:21])=[CH:16][CH:15]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].O.[OH-].[Li+].Cl>O1CCCC1>[CH:1](/[C:14]1[CH:15]=[CH:16][C:17]([CH:18]=[CH:19][C:20]([OH:22])=[O:21])=[CH:24][CH:25]=1)=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 70432516HCID 70432516, compound

Product 1

HCID 70432418HCID 70432418, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-[(E)-1-tridecenyl]cinnamate (342 mg, 1 mmole from Example 16 in 50% aqueous tetrahydrofuran (25 ml) was added lithium hydroxide monohydrate (420 mg, 10 equivalents) and the mixture was stirred at room temperature overnight. The cloudy mixture was acidified with dilute hydrochloric acid and extracted with ether. The extracts were washed with brine, dried (magnesium sulphate) and evaporated to a white crystalline solid. Yield 330 mg (100%). Recrystallisation from methanol afforded material of mp 107° C., νmax (mull) 2600 (broad), 1710, 1680, 1625, 1425, 1308, 1285 cm-1 ; δ(DMSO-d6) 0.82 (3H, distorted t, CH3), 1.25 (18H, m. alkylene chain), 2.18 (2H, m, allylic CH2), 6.37 (2H, distorted s), 6.48 (1H, d, J 15 Hz, C=CHCO2), 7.52 (4H, AB quartet, J 7.5 Hz, Δν 18 Hz, aromatics), 7.60 (1H, d, J 15 Hz, ArCH=C--CO2) λmax (MeOH) 307 (31,200), 226 (12,200) nm.

Workup

  1. extractionextracted with ether
  2. washThe extracts were washed with brine
  3. dry with materialdried (magnesium sulphate)
  4. customevaporated to a white crystalline solid
  5. customRecrystallisation from methanol afforded material of mp 107° C., νmax (mull) 2600 (broad), 1710, 1680, 1625, 1425, 1308, 1285 cm-1

Sources & evidence

ORD record
ord-afa0637880bf4d82bede3b6b7860ed10
Source dataset
uspto-grants-1987_12
Patent number
US04713486

Reaction notes

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